Potassium Carbonate → (2-Fluoro-phenyl)-[4-(4-nitro-isoquinolin-1-yl)-piperazin-1-yl]-methanone

HRID 729617Notes

Reaction equation

HRID 729617 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:9].C([O-])([O-])=O.[K+].[K+].Cl[C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([N+:33]([O-:35])=[O:34])=[CH:25][N:24]=1>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([N:10]1[CH2:11][CH2:12][N:13]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]([N+:33]([O-:35])=[O:34])=[CH:25][N:24]=2)[CH2:14][CH2:15]1)=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 544862(2-Fluoro-phenyl)-piperazin-1-yl-methanoneHCID 227654811-Chloro-4-nitroisoquinoline

Product 1

HCID 69055062(2-Fluoro-phenyl)-[4-(4-nitro-isoquinolin-1-yl)-piperazin-1-yl]-methanoneYield 75.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add (2-fluoro-phenyl)-piperazin-1-yl-methanone (3.16 g, 12.9 mmol) and K2CO3 (8.9 g, 64.5 mmol) to 1-chloro-4-nitroisoquinoline (2.85 g, 13.7 mmol) in acetonitrile (100 mL) and stir for 24 hours. Filter the insoluble solid and wash the cake with AcOEt. Evaporate the solvent under reduced pressure to give a residue. Subject residue to silica gel chromatography eluting with hexane:AcOEt 20-90% to give 3.72 g of (2-fluoro-phenyl)-[4-(4-nitro-isoquinolin-1-yl)-piperazin-1-yl]-methanone as a solid. LCMS ES+(m/z) 381.2 [M+H].

Workup

  1. filtrationFilter the insoluble solid
  2. washwash the cake with AcOEt
  3. customEvaporate the solvent under reduced pressure
  4. customto give a residue
  5. washSubject residue to silica gel chromatography eluting with hexane

Sources & evidence

ORD record
ord-26eeef3bb3aa40daadd9e681add3e188
Source dataset
uspto-grants-2009_09
Patent number
US07582638B2

Reaction notes

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